Double negative grammar

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Hopefully somebody here can help solve a workplace dispute: is it an example of bad grammar to use the term "least bad", i.e. "If we had to lose a document, these were the least bad ones to lose." A colleague used this the other day and insists that this is not grammatically incorrect, however I beleive that it should be "If we had to lose a document, these were the best ones to lose." As we are both accountants (and I ahve a maths degree) I wouldn't want to trust either one us in matters relating to grammar, so any help would be greatly appreciated.
 

Anglika

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There is a subtle semantic difference!

All the documents are bad to lose; some are more so than others.

If any documents are to be lost, these are the best to lose - the least important ones.

I incline to go with your colleague on this one.;-)
 

susiedqq

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I think the meaning is: Of all of the documents, these were the ones to lose that would result in the least damage.

So I would say: "If we had to lose a document, this was the one to lose." (or . . . "lose documents, these were the ones to lose")

I am reminded of the famous line from Casa Blanca: "Of all the gin joints . . . "
 
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